One more question about OTL figures (all born prior to 1922)...
Stanley Baldwin
Neville Chamberlain
Lord Halifax
Bernard Law Montgomery
Herbert Chapman
Matt Busby
Bill Shankly
I will begin my answer with a caveat: I am unsure of the precise details of the British political situation in TTL prior to the rise of the Conservative-Silver Shirt coalition in the 1930s. I am making the assumption that domestic politics in the United Kingdom was affected by the military and territorial losses in the First Great War, along with postwar economic problems and labor unrest. Other interpretations of TTL’s careers of Stanley Baldwin, Neville Chamberlain, Lord Halifax, and Bernard Law Montgomery may exist in the “Filling in the Gaps” or TL-191 thread. The following represents, then, one speculative scenario for the public figures named in your question.
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Stanley Baldwin had a roughly similar political career, until the immediate years following the First Great War. In TTL, the British military defeat in the FGW in 1917 also led to the collapse of the wartime coalition between the Conservative Party and the Liberal Party. In the first postwar general election, the Labour Party, led by William Adamson, ultimately triumphed. However, Adamson’s government was weakened by continuing economic problems and growing unrest from the trade unions. The rule of law in Britain was also negatively affected in the immediate postwar years by the appearance of far-right groups, some of which were also led by FGW veterans. Some of these groups were utilized as strike-breakers, while other groups of this nature engaged in street fighting with anyone and any group imagined as an enemy.
During this time, Stanley Baldwin achieved leadership over the Conservative Party, and ultimately led the party to victory in a general election called in 1923. Baldwin focused on attempting to stabilize the British economy, made worse in TTL by reparations demands by the Central Powers. One of the seminal events of Baldwin’s tenure in government was the General Strike of 1925, analogous to our world’s General Strike of 1926.
As in our world, this General Strike affected the coal industry and transport, and was sparked by plans to reduce the wages of coal miners. Unlike in our world, the General Strike of 1925, which resulted in several weeks of disruptions to transportation in the United Kingdom in April-May 1925, was accompanied by a not-insignificant level of violence, both due to the responses by the police towards striking workers, and due to clashes throughout the country between far-right and far-left groups. As in the case of a number of interwar far-right groups, many far-left groups engaged in street violence were originally founded by veterans.
Baldwin’s government was gravely weakened by the 1925 General Strike, with Baldwin himself increasingly blamed by the general public for a breakdown of law and order, persistent economic problems, and the sense of national humiliation. Baldwin also faced a groundswell of anger from within his own party, with some Conservative figures in the government and the media accusing him of failing to take harsher action against the trade unions involved in the General Strike. Some historians have claimed that Winston Churchill’s own radicalization, and subsequent willingness to align himself with the Silver Shirts, can be dated to this period. Baldwin, weakened politically, led the Conservatives to defeat in the general election of 1927, to a resurgent Labour Party led by Ramsay MacDonald.
Baldwin attempted to maintain leadership of the Conservative Party as leader of the opposition to MacDonald’s government. However, he faced constant criticism from a growing number of far-right backbenchers from his own party. The stabilization of the British economy in the late 1920s, facilitated by the renegotiation of reparations to the Central Powers, led some in Britain to speculate that the Labour Party would hold power for some time to come.
It was during this era that Oswald Mosley successfully orchestrated the merger of a large number of smaller far-right groups into the Silver Shirt party.
The 1931 Business Collapse fatally weakened the Labour government. However, Baldwin would be unable to take advantage of these political developments. He was ousted as leader of the Conservative Party in an MP-led revolt led by Winston Churchill, who subsequently made the fateful decision to ally the Conservatives with the Silver Shirts, who appeared to enjoying a surge of support in traditional Conservative constituencies.
Baldwin resigned from Parliament following his ouster as party leader, and played no role in the Conservative-Silver Shirt Coalition that emerged following the 1932 general election. He grew to be horrified by the measures taken by the Coalition against its claimed “enemies” and the sharp curtailment of political freedoms. Baldwin kept his own views private. He died in 1947, and was said to have been a broken man, in the wake of Britain’s defeat in the SGW and the three German superbombings.
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Neville Chamberlain’s political career diverged from OTL beginning in the FGW, when he was not offered a position by the wartime coalition. However, he was still ultimately elected to Parliament, and eventually became a close ally of Stanley Baldwin. Chamberlain focused on issues relating to public health, but never became Minister of Health. Chamberlain’s political career collapsed in 1931, with Baldwin’s ouster as leader of the Conservatives, resulting in his retirement from politics. Unlike Baldwin, Chamberlain did not keep his objections to the Coalition, and its increasingly repressive domestic policies, private. Chamberlain was not arrested, but did receive a not-so-subtle warning that remaining in Britain would be detrimental to his health. Chamberlain left Britain with his family for New Zealand, where he died in 1940.
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In the TL-191 series, Lord Halifax is shown to be the British ambassador to the Confederacy. After the end of the SGW, Halifax’s political career ended. The US government, under the Dewey administration, initially considered formally requesting the British government that Halifax be handed over, after learning of his role in facilitating the Confederacy’s superbomb project, but ultimately decided against such a request. Halifax did write a memoir of his time as ambassador to the CSA, which was surprisingly scathing both of Featherston and the CSA in general; Halifax concluded this memoir by stating that it had been a great mistake for Britain ever to have supported the CSA in any capacity. Lord Halifax died in 1959.
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Bernard Law Montgomery survived the FGW. His experiences during the war convinced him of the need for the British military to modernize its doctrines concerning armored warfare. His military career would later be bolstered by the policies of the Conservative-Silver Shirt Coalition, which pursued a policy of rearmament and actively sought out innovative military commanders. By the time war broke out in 1941, Montgomery found himself as one of the British frontline commanders on the Western Front. His successes on the battlefield in the Low Countries and in north Germany did not go unnoticed by his superiors, though he was not ultimately put in a position of supreme command. Montgomery did himself no political favors by publicly objecting to the Entente attack on Norway, believing it to be a waste of resources. While Montgomery was not arrested due to this objection, he was removed from his position as a frontline commander and demoted. Montgomery found himself leading his men on a steady retreat from north Germany and through the Low Countries. The forces under his command were among those evacuated home to Britain following the end of the war in 1944. Montgomery was subsequently discharged from the British Army. However, his military career was not over; Montgomery accepted an offer by an Australian representative of a position of command in the Australian military. Montgomery, along with a number of other recruited ex-British military commanders, would play a key role in Australia’s postwar program of military expansion and modernization, amidst fears of a future Japanese invasion.
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Herbert Chapman’s life and career was not dramatically different from OTL until the 1930s, when he did not die of pneumonia, as in our world. He continued to enjoy a successful career as manager of the Arsenal Football Club. Tragically, he was killed in 1944, in the German superbomb attack on London.
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Matt Busby’s family immigrated to Australia in the mid-1920s, following the 1925 General Strike and related political violence. He eventually found work in an arms factory, where he remained until the end of the SGW. His talents in organization and management did not go unnoticed, and he was among those recruited to work in the Oceania arms manufacturing company. He rose through the ranks at Oceania, and eventually served on the company’s board of directors, before his retirement in 1989.
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William Shankly’s analogue in TTL served in the Royal Air Force. After the end of the SGW, he accepted an Australian offer of recruitment into the Australian Air Force. He was retired from active military service, however, by the time of the Fourth Pacific War in 1967. A lifelong football enthusiast, Shankly jumped at the opportunity to work in the front office for the South Melbourne Football Club (the Swans), his adopted football team.